1,4-Butanediol → 5-bromo-4-chloro-2-(4-hydroxy-butoxy)-N-methyl-N-pyridin-2-yl-benzenesulfonamide

HRID 1891390Notes

Reaction equation

[CH2:1]([OH:6])[CH2:2][CH2:3][CH2:4][OH:5].[H-].[Na+].[Br:9][C:10]1[C:11]([Cl:28])=[CH:12][C:13](F)=[C:14]([S:16]([N:19]([CH3:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)(=[O:18])=[O:17])[CH:15]=1>CN(C=O)C>[Br:9][C:10]1[C:11]([Cl:28])=[CH:12][C:13]([O:5][CH2:4][CH2:3][CH2:2][CH2:1][OH:6])=[C:14]([S:16]([N:19]([CH3:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)(=[O:17])=[O:18])[CH:15]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 1,4-butanediol (0.315 mL, 3.6 mmol) in DMF (2.5 mL) at ambient temperature was added sodium hydride (60%, 34 mg, 0.85 mmol) and the mixture was stirred for 15 minutes. A solution of 5-bromo-4-chloro-2-fluoro-N-methyl-N-pyridin-2-yl-benzenesulfonamide (0.268 g, 0.71 mmol) in DMF (2.5 mL) was added and the mixture heated at 50° C. for 2 h. The solvent was removed in vacuo and water and DCM were added. The mixture was extracted with DCM. The organic layer was washed with brine and was dried over anhydrous MgSO4. Concentration of the filtrate provided a residue that was purified by silica gel chromatography [eluent: 50% ethyl acetate in hexane] to afford 5-bromo-4-chloro-2-(4-hydroxy-butoxy)-N-methyl-N-pyridin-2-yl-benzenesulfonamide as a solid (0.309 g). MS: 451.0 (M+H)+; tR=2.59 min (method 1).

Workup

customThe solvent was removed in vacuo and water and DCM
additionwere added
extractionThe mixture was extracted with DCM
washThe organic layer was washed with brine
dry with materialwas dried over anhydrous MgSO4
customConcentration of the filtrate provided a residue that
customwas purified by silica gel chromatography [eluent: 50% ethyl acetate in hexane]

Sources & evidence

ORD record: ord-47980c8d7a534ada919db95e4d025a59
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08507536B2

Reaction notes

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